Ethanol → HCID 25261906, compound

HRID 383285Notes

Reaction equation

HRID 383285 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([OH:9])[CH3:8].Cl[C:11]1[CH:16]=[C:15]([C:17]2[N:21]3[CH:22]=[C:23]([NH:26][CH:27]4[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:14]=[CH:13][N:12]=1>CS(C)=O.O>[CH2:7]([O:9][C:13]1[CH:14]=[C:15]([C:17]2[N:21]3[CH:22]=[C:23]([NH:26][CH:27]4[CH2:28][CH2:29][CH:30]([OH:33])[CH2:31][CH2:32]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:16]=[CH:11][N:12]=1)[CH3:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 10796Cesium carbonateHCID 252619024-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

Product 1

HCID 25261906HCID 25261906, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Cs2CO3 (5 eq, 1.45 mmol, 480 mg) and 4A molecular sieves (400 mg) are stirred in a mixture of DMSO (5 ml) and ethanol (5 eq 0.8 ml). To this suspension is added [4-[3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol (Example 2.1) (1 eq, 100 mg, 0.29 mmol). The reaction is heated at 120° C. for 16 hours. The mixture is diluted with H2O (20 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo to give a blue oil. The residue is purified by flash chromatography on silica eluting with 0-10% methanol in EtOAc The resulting residue is loaded onto a SCX-2 cartridge (resin loading 0.67 mmol/g) eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+=353

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a blue oil
  6. customThe residue is purified by flash chromatography on silica eluting with 0-10% methanol in EtOAc The resulting residue
  7. washeluting with MeOH
  8. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  9. customdried under vacuum

Sources & evidence

ORD record
ord-e3902bc4856d42dbb7c16638aa124767
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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